Trimethylsilyl acetylene compounds, their preparation and their

Details Trimethylsilyl acetylene compounds, their preparation and their Trimethylsilyl acetylene compounds, their preparation and their

1990-02-01

1992-01-07

Nutter, Nathan M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

552201, C07H 1524

Patent

active

050793497

ABSTRACT:
The invention relates to novel compounds of the formulae ##STR1## wherein S is H, alkyl or alkoxy and R is a good leaving group, and to the preparation of these compounds in a stereospecific manner to obtain a configuration wherein OH at C-3 and OR at C-1 are in the cis-position, which compounds can be used for the synthesis of daunomycinone and derivatives thereof.
Daunomycinone can be used for the preparation of daunomycin and adriamycin.

REFERENCES:
Suzuki et al "A Novel Synthesis of the .alpha.-Hydroxyketone Moiety of Anthracyclinones by the Use of 2-Trimethylsilylethynylcerium (III) Reagents" Chemistry Letters, pp. 1543-1546, 1984.
Kelley et al "An Efficient, Regiospecific Synthesis of (.+-.)Daunomycinone" Tetrahedron, vol. 40, No. 22, pp. 4569-4577, 1984.
Gupta et al "An Efficient Enantiocontrolled Synthesis of (.+-.-4-Demethoxydaunomycinone" Tetrahedron, vol. 40, No. 22, pp. 4657-4667, 1984.
Angelo et al "Utilisation D'Alkoxyacetates Chiraux-Equivalents De L'Hydroxyacetaldehyde--En Aldolisation Stereocontrolee" Tet. Letters 24(52) 5869, 1983.
Krohn et al "Totalsynthese des Daunomycinons" Chem. Ber. 112, 3453-3471 (1979).

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